Be the CEO of Your Retirement
CEOs have some specific skills and habits that make them successful business leaders. The rest of us can take a few pages from their playbooks to make our retirement plans a success as well.
In my 33 years as a financial professional, I’ve been privileged to meet and get to know a number of CEOs.
What I’ve found is, as you might expect, they tend to be smart people. But I’ve also discovered something else about them when it comes to investing: They have different habits than many other clients.
They fall into the category of what I affectionately call “busy” clients. They take an active role in all aspects of their investments and leave little to chance. One of these “busy” clients routinely calls me to ask: “What can we be doing differently?” Another will wonder: “What is the smart money up to?”
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
The point is they aren’t passive, letting their retirement plans be buffeted by whatever economic winds blow through. They are thinkers, taking the same traits, habits and vision that make them effective in running a company, and applying those to the way they manage their investment portfolios.
What works for them also can work for you. You can (and should) be the CEO of your retirement. Here are a few tips for getting started in that direction:
Set performance goals.
CEOs know things don’t just happen. They understand their company and the individuals within it all need performance goals if they and the business expect to thrive. You need goals with your retirement planning as well. Maybe it’s a particular retirement age you’re aiming for. Maybe it’s a specific amount of savings you need to make retirement work. You should set goals and, like any good CEO, be prepared to make adjustments if your expectations aren’t being met.
Question everything.
CEOs like to ask questions because they need information — lots of information — to make decisions that will affect the health and future of the organization. Being inquisitive is important to you and your retirement as well. So ask away. What’s the performance history of your investments? What fees are you paying and how much are they? Is there an investment strategy you haven’t tried that’s worth considering? How much should you expect to withdraw each month from your savings during retirement?
Be willing to adapt.
A successful CEO needs to be open to new ideas and new concepts; otherwise, they get left behind while their competitors flourish. You aren’t so much worried about competitors when it comes to your retirement, but you do need to be willing to adapt when necessary as factors related to you specifically, or the economy in general, change. For example, as you age, you’ll want to look at reducing the risk in your portfolio. The aggressive investment strategy that made sense when you were 35 is probably too big of a gamble when you are five to 10 years away from retirement.
Take the job seriously.
You can bet CEOs take what they do seriously. (One study by Harvard professors found CEOs work an average of 62.5 hours per week.) No, you probably don’t need to put in 62.5 hours a week planning your retirement. But you do need to take things seriously as you consider investment options, your retirement timeline, when it’s best to begin drawing Social Security, and anything else that might come into play. After all, it’s your retirement and future at stake.
Look at the big picture.
It’s easy to let whatever is happening at the moment command your attention. This problem needs solving — now. That opportunity presents itself — now. But top CEOs aren’t just preoccupied with the present. Far from it. They spend as much as 50% of their time thinking about the long-term future. You might not need to divide your time in quite the same way, but you do need to give serious thought to a few topics that will be part of your long-term retirement future. If things like health care, insurance and estate planning have been in the junk drawer of your financial plan, ignored while you deal with pressing issues of the day, it’s time to take them out and do a deep dive into them. You might be surprised what improvements you can make.
The bottom line is CEOs do things differently; that’s one of the reasons they end up being CEOs. They are charged with creating and maintaining the success of a company, so if they don’t develop certain habits and ways of thinking they risk failure.
In much the same way, even when you seek the advice of a financial professional, you ultimately remain in charge of your retirement. As the CEO, it falls to you to make sure you achieve the success you need to make retirement a fulfilling and relaxing time.
-
Ask the Editor: Tips for Filing Your 1040Ask the Editor In this week's Ask the Editor Q&A, Joy Taylor answers questions on preparing and filing your 2025 Form 1040.
-
Is Direct Primary Care Right for Your Health Needs?With the direct primary care model, you pay a membership fee for more personalized medical services.
-
Smart Ways to Share a Credit CardAdding an authorized user has its benefits, but make sure you set the ground rules.
-
If You're in the 2% Club and Have a Pension, the 60/40 Portfolio Could Hold You BackIncome from your pension, savings and Social Security could provide the protection bonds usually offer, freeing you up for a more growth-oriented allocation.
-
Bye-Bye, Snowbirds: Wealthy Americans Are Relocating Permanently for Retirement — and This Financial Adviser Can't Fault Their LogicWhy head south for the winter and pay for two properties when you can have a better lifestyle year-round in a less expensive state?
-
Consider These 4 Tweaks to Your 2026 Financial Plan, Courtesy of a Financial PlannerThere's never a bad time to make or review a financial plan. But recent changes to the financial landscape might make it especially important to do so now.
-
We Know You Hate Your Insurance, But Here's Why You Should Show It Some LoveSure, it's pricey, the policies are confusing, and the claims process is slow, but insurance is essentially the friend who shows up during life's worst moments.
-
Is a Caregiving Strategy — for Yourself and Others — Missing From Your Retirement Plan?Millions of people over 65 care for grandkids, adult kids or aging parents and will also need care themselves. Building a caregiving strategy is crucial.
-
6 Financially Savvy Power Moves for Women in 2026 (Prepare to Be in Charge!)Don't let the day-to-day get in the way of long-term financial planning. Here's how to get organized — including a reminder to dream big about your future.
-
Private Equity Is Fundamentally Changing: What Now for Investors and Business Owners?For 40 years, private equity enjoyed extraordinary returns thanks to falling rates and abundant credit. That's changed. What should PE firms and clients do now?
-
I'm a Real Estate Expert: 2026 Marks a Seismic Shift in Tax Rules, and Investors Could Reap Millions in RewardsThree major tax strategies will align in 2026, creating unique opportunities for real estate investors to significantly grow their wealth. Here's how it works.
